Vacation rentals in Cumberland

An outdoor picnic table crafted from weathered wood is positioned on a grassy area beside the cottage. Natural light illuminates the scene, highlighting the table's rustic charm. A window with sheer curtains is visible in the background, framed by treetops.

4.94 out of 5 average rating, 252 reviews

Jacob's Cottage

Free WI-FI now available. Our place is good for couples, solo adventurers, business travelers and families (with kids). The Cottage is a quaint, Cape Cod style house built in 1950. It sits high on a hill in the heart of Maryland's Appalachian Mountains in Allegany County. It is surrounded by views of Wills Mountain and Shrivers Ridge. The Cottage sits amongst a 660 acre family managed forest. Visitors have spotted deer, turkey, rabbits, squirrels, black bear and a multitude of song birds.

An aerial view captures a charming town at dusk, featuring historic buildings and church spires. Streets are illuminated by warm lights, guiding the eye through the layout. A river flows beneath the bridge, surrounded by trees, creating a serene landscape.

5 out of 5 average rating, 107 reviews

NEW LISTING-"Cumberland Cottage"-charming,quaint

Relax in this charming, renovated rancher in a peaceful setting. Located outside of the city limits but convenient to attractions and dining. This home is comfy with all the amenities you have in your own home. Outside area for your children to play or for you to relax on the back porch. Cumberland is in easy driving distance to PA and WV. Enjoy cooking together and dining or playing games in the dining room, then relaxing in the living area. Renovated but still keeping the charm of a rancher.

4.95 out of 5 average rating, 57 reviews

A blue tufted sofa features decorative buttons and rests on a striped area rug. A patterned cushion and a solid yellow cushion add texture, while a white bedding set can be seen in the background against a light gray wall.

Loft in Cumberland

Historical loft, 2 Blocks from Trail & Downtown

When you enter your loft apartment you will have an interior space to secure your bikes. After a fun day on the C&O or GAP trail you will enjoy a shower, a cup of local Basecamp coffee, and restful sleep Conveniently located 2 blocks off a trail entrance. Downtown restaurants only a 5 minute drive Included in your room is a kitchen sink, microwave, fridge/freezer, toaster and 12 cup coffee pot with local Basecamp coffee in regular & decaf, & tea Keyless entry, entire place to yourself

4.99 out of 5 average rating, 464 reviews

The exterior of a bistro is displayed, featuring a vibrant red façade. The name 'Mise en Place' is prominently shown above the entrance. An American flag and a French flag hang from the awning, while high-top chairs stand outside, inviting patrons to enjoy the ambiance.

Apartment in Cumberland

Steeple View Flat in Historic District

Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.

4.99 out of 5 average rating, 184 reviews

The image captures a spacious parking area designed for several vehicles, with three cars parked and a scenic view of a city in the background. Green trees and shrubs frame the space, promoting a peaceful atmosphere. The hills and mountains provide a serene backdrop to the retreat.

Cottage in Cumberland

The Cottage on the Hill

Nestled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in one of your reserved spaces and step down to a unique retreat high above the city to enjoy a vintage cottage with modern amenities. Walk to Historic Cumberland, enjoy local and regional attractions, or stay in and grill, build a fire, or play pool, poker, board or yard games. Well appointed, fully equipped, and with a beautiful view, come relax and enjoy this one of a kind location.

A steam locomotive, numbered 734, rests on the tracks with billowing smoke rising from its chimney. The train features a shiny black exterior with gold accents, while the historic station building is visible in the background, showcasing red brick architecture and arched windows.

4.84 out of 5 average rating, 157 reviews

Charming 1907 Home in Historic Downtown Cumberland

This charming 1907 home is located just blocks from the main pedestrian street in Historic Downtown Cumberland and a 10 minute walk from Canal Place, the C&O Canal Great Allegheny bike trails, and the Western Maryland Scenic Railroad. The remodeled interior is equipped with all the modern conveniences, including a large kitchen and bathroom with large tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.

5 out of 5 average rating, 107 reviews

A set of wooden steps with a textured finish leads up to the entrance of the log cabin. Handrails made of sturdy timber provide support, while the surrounding greenery adds natural appeal. The cabin's wooden door can be seen, enhancing the rustic charm.

Cabin in Springfield

1832 Historic Washington Bottom Farm Log Cabin

Welcome to our renovated 1832 Log Cabin on our 300+acre Certified Organic farm. Guests can use our river frontage to fish, canoe, kayak, tube, or gather by the fire pit. We have mountain views, dark night skies revealing stars, planets, and the Milky Way, plus great sunsets. Wildlife includes deer, fox, bear, turkey, eagles, and owls, to name only a few. Lots of History here: site of a French & Indian fort, an early Indian Burial Mound, and the Hosts' historic plantation home.

4.96 out of 5 average rating, 229 reviews

A quaint cabin is nestled among lush greenery, showcasing wooden siding and a slanted roof. A spacious deck extends from the front, featuring rocking chairs and surrounded by a tranquil forest setting, inviting a peaceful retreat in nature.

Cabin in Paw Paw

Easygoing

Tired of the chaos and need a place to unwind and relax ? We have the perfect place for you! A quaint, quiet cabin to let you clear your mind and spirit after a day of hiking, biking or kayaking since we are only five miles from both the Paw Paw tunnel and the Potomac river. The cabin is equipped with electric, heating, stove top, microwave, large deck, hammock chairs, horseshoe pit, 2 double size futons with room to spare, indoor toilet but BEST of all is showering outside!

A shelf displays a collection of children's toys and books. A green toy tractor sits alongside a colorful container of building blocks. Various children's books are stacked, and a game of bean bag toss is visible in the back, indicating family-friendly amenities.

4.89 out of 5 average rating, 541 reviews

Cumberland Street House -GAP trail perfection!

Cyclists dream come true! The Cumberland Street House is less than a quarter mile from the Great Allegheny Passage - perfect for large groups! All of Cumberland's charm within walking distance. Downtown restaurants and shops only a half a mile away. Historic district, Cumberland Theatre & Western Maryland Scenic Railroad are just around the corner. Bikes can easily be stowed in the back room off the kitchen. Easy parking, and fenced-in yard is great for kids and pooches.

A rugged rock formation features textured cliffs rising against a backdrop of bright blue sky. Vibrant autumn foliage in shades of orange and yellow surrounds the base, contrasting with the gray stone. Scattered clouds add depth to the scene, capturing the essence of a fall day.

4.9 out of 5 average rating, 107 reviews

Queen City Quarters- cozy, historic, 1920s home

Stay in a quiet setting as you explore Cumberland, MD. Enjoy a day trip on the nearby, scenic, steam train. Bike the Gap and C&O trail, minutes away. Explore the restored historic downtown with shopping and restaurants. This space is not suitable for small children or those with mobility concerns. No large groups or parties. Bedroom doors are louvered doors. See pictures. Research city and area if you are unfamiliar with economic conditions. We have a bike rack for 3 bikes.

4.86 out of 5 average rating, 303 reviews

The historic building features a red brick facade with multiple stories and large windows. Banners are displayed across the front, and the entrance is highlighted by awnings. Street-level storefronts are visible, along with decorative elements that add character to the architecture.

Home in Frostburg

Allegany Connection

NOTICE: extra santizing of hand touching areas in place for your protection. This eclectic 2-story duplex, late 18th century structure has both old and new charm. Single BR & bath upstairs; LR and Kit downstairs. Only 1 block from Main St. restaurants & unique shops. All are welcomed. Please bring your own infant bed. Sorry no pets. Free reserved parking for 1 vehicle & fast Wi-Fi. Instant booking is on. ABSOLUTELY NO SMOKING, or any kind is permitted inside our home.

4.92 out of 5 average rating, 126 reviews

A bathroom sink area features a clean, white basin with a chrome faucet. A small glass vase filled with artificial white flowers adds a touch of decor. Essential toiletries are neatly arranged beside the sink, with a roll of white towels hanging for easy access.

Townhouse in Cumberland

The Shadoe on Greene

Just a stones-throw from everything Cumberland has to offer, The Shadoe on Greene is at the heart of it all. Literal steps from the Western Maryland Scenic Railroad, the Great Allegheny Passage trail & the Historic City Center, with a wide array of local shops and eateries. This unique property was built in the 1850's and has been lovingly restored to embrace it's history, as well as provide all of the modern amenities you'd expect.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

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A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Cumberland vacation rentals

Laptop-friendly workspace

Other great vacation rentals in Cumberland

Superhost

The kitchen area features a wooden island with bar stools and a granite countertop. Cabinets are positioned above and below the countertop, while modern appliances are visible. A ceiling fan hangs above, and warm wooden flooring is present throughout the space.

Apartment in Midlothian

4.82 out of 5 average rating, 11 reviews

Studio Apartment near FSU

5 out of 5 average rating, 23 reviews

A wooden table is adorned with decorative items, including a candle in a glass holder and a planter featuring vibrant succulents. A small set of metallic cups is presented in a holder, with a backdrop of colorful buildings visible through the window.

Apartment in Cumberland

Downtown Cumberland Jewel

5 out of 5 average rating, 22 reviews

A modern kitchen space is presented, featuring stainless steel appliances and white cabinetry. Countertops are adorned with small kitchen items and a decorative basket. Two light fixtures hang above, while textured floor mats provide a soft touch beneath.

Home in La Vale

CJ’s Escape Great location & just like home

A wooden staircase with a metal railing leads to the upper level. The steps are framed by light gray walls and a decorative molding. Natural wood flooring is visible at the base, adding warmth to the space.

4.94 out of 5 average rating, 96 reviews

Great Location, Spacious, Comfy 2 bdrm 3 bed home

5 out of 5 average rating, 37 reviews

The exterior features a vibrant yellow door complemented by a stone foundation and gray siding. Two tall windows with white trim allow natural light to enter, while a decorative light fixture is mounted beside the door. A concrete pathway leads to the entrance.

Apartment in Bedford

Private Studio Apartment - Own Entry

4.93 out of 5 average rating, 61 reviews

A welcoming entrance is displayed, featuring a solid brown door adorned with a seasonal floral wreath. A wooden rocking chair with striped cushions is placed beside a small table. Potted plants add greenery to the area, enhancing the cozy vibe of the stone facade.

Cabin in Keyser

Bobby Joes Cozy Little Cabin, LLC